Antimycobacterial derivatives of tetrazole

Waisser, Karel; Vanzura, J; Hrabálek, Alexandr; Vinšová, Jarmila; Gresak, S.; Hruška, Jiří; Odlerová, Z

doi:10.1135/cccc19912389

Cited by 8 publications

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“…The synthesis of tetrazole acetamides via azide-coupling method is shown in Schemes 1-3. The reaction of 1-phenyl-4,5-dihydro-1H-1,2,3,4-tetraazole-5-thione (1) with chloroethyl acetate in the presence of K 2 CO 3 furnished the regioselective S-alkylation reaction product 4 [13,14]. The expected S-alkylation reaction was favored because of an interaction between the HOMO of the nucleophile and the LUMO of the electrophile to produce the Sattack [13].…”

Section: Resultsmentioning

confidence: 97%

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Efficient synthesis of 1‐substituted‐4‐phenyl‐1, 4‐dihydro‐5H‐tetrazole‐5‐thione and (1‐phenyl‐1H‐tetrazol‐5‐yl)thioacetyl derivatives

Fathalla

Ali

2007

Heteroatom Chemistry

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Section: Resultsmentioning

confidence: 97%

“…• C. [14]. To a solution of the ester derivatives 4 (1.78 g, 0.01mol) in absolute ethyl alcohol (30 mL), hydrazine hydrate (0.74 mL, 0.015 mol) was added and the reaction mixture was heated under reflux for 3 h. The reaction mixture was cooled and evaporated under reduced pressure till dried.…”

Section: Ethyl[(1-phenyl-1h-tetrazol-5-yl)thio] Acetate (4)mentioning

confidence: 99%

Efficient synthesis of 1‐substituted‐4‐phenyl‐1, 4‐dihydro‐5H‐tetrazole‐5‐thione and (1‐phenyl‐1H‐tetrazol‐5‐yl)thioacetyl derivatives

Fathalla

Ali

2007

Heteroatom Chemistry

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“…Various nitrogen containing heterocycles have been recently studied for their antibacterial or antimycobacterial effects, e.g. 3,5-dinaphthyl-2-pyrazolines [ 4 ], 2-phenyl-5,5-dialkylimidazolinones [ 5 ], 4-amino-5-aryl-1,2,4-triazoles [ 6 ], triazolo- or tetrazolopyrrolopyrimidines [ 7 ], 5-alkylsulfanyl-tetrazoles [ 8 , 9 , 10 , 11 ], benzimidazoles [ 12 ], 1,3-benzoxazinediones [ 13 , 14 , 15 ], quinazolines [ 14 , 16 , 17 , 18 , 19 ], and quinoxalines [ 20 , 21 ]. Reviews of antimycobacterially active derivatives containing one or more nitrogen atom in the five- or six-membered ring have been published [ 16 , 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Quinazoline-4-thiones

et al. 2003

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Several 2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thiones and 2-methyl-3-phenylquinazoline-4(3H)-thiones were synthesized and tested for their antimycobacterial, photosynthesis-inhibiting, and antialgal activity. Antimycobacterially active compounds were found among the 6-chloro substituted compounds. 6-Chloro-3-(4-isopropylphenyl)-2-methylquinazoline-4(3H)-thione exhibited higher activity than the isoniazid standard against Mycobacterium avium and M. kansasii. Most of the compounds possessed photosynthesis-inhibiting activity. 6-Chloro-2,2-dimethyl-3-phenyl-1,2-dihydro-quinazoline-4(3H)-thione and its 3´-chloro- and 3´,4´-dichloro analogs were most effective in the inhibition of oxygen evolution rate in spinach chloroplasts. Of compounds selected for toxicological screening, 6-chloro-3-(4-isopropylphenyl)-2-methyl-quinazoline-4(3H)-thione was the only one active in the brine shrimp bioassay.

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A signifi cant attention was paid to the development of effi cient synthetic procedures for 5-(R-sulfanyl)tetrazoles (R = Alk, Bn) [1].

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confidence: 99%

New method of 5-mercaptotetrazoles functionalization

2011

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Tetrazole derivatives containing a sulfur atom in the position 5 of the ring are promising as biologically active compounds and also as components of photomaterials [1][2][3][4]. At the same time the mercaptothiazoles are effi cient reagents in the schemes of the total synthesis of natural substances [4].A signifi cant attention was paid to the development of effi cient synthetic procedures for 5-(R-sulfanyl)tetrazoles (R = Alk, Bn) [1]. The traditional methods of preparation of these compounds are based on the alkylation of 5-mercaptotetrazoles with various electrophilic agents [1,2].The preparation methods of 5-(R-sulfanyl)tetrazoles (R = Ar) are poorly understood. A synthesis was reported of 5-arylsulfanyltetrazoles by the direct arylation of 5-mercapto tetrazoles by fluoro(chloro)nitrobenzenes [5], by the reaction of 5-mercaptotetrazoles with phenols under electrolysis conditions [6], and also by the reaction of 5-tosyltetrazoles with thiophenols [7]. These methods are not general for they make it possible to obtain 5-arylsulfanyltetrazoles only with defi nite substituents (R = Ar). Besides the necessity to use diffi cultly available reagents and special equipment, long reaction time and relatively low yield of target compounds reduce the effi ciency of the cited methods.Therefore the development of a general and effi cient method of the synthesis of 5-арилsulfanyltetrazoles is an urgent problem.At present one of the most promising methods of synthesis and functionalization of aromatic thioethers is their direct arylation with aryl halides catalyzed by palladium and copper complexes [6].We found that the arylation of 1-phenyl-5-mercaptotetrazole (I) with iodobenzene catalyzed by CuI (10 mol%) in the presence of a ligand (2 equiv of ethylenediamine) and a base (2 equiv of Cs 2 CO 3 ), made it possible to obtain 5-phenylsulfanyltetrazole (II) in a high yield (see the scheme).The developed method of the sysnthesis of 5-arylsulfanyl-tetrazoles can be used for the synthesis of 5-(R-sulfanyl)tetrazoles (R = Vin, Ht). By the Сu-catalyzed vinylation and hetarylation tetrazole I we obtained sulfanyltetrazoles III and IV in the yields of 92 and 85% respectively (see the scheme).Note that in contrast to the method of direct arylation of mercaptotetrazoles [5] the Cu-catalyzed arylation allows the preparation also of the other 5-(R-sulfanyl) tetrazoles with R = Vin and Ht, and also does not require the use of rare reagents and additional equipment.Synthesis of tetrazoles II-IV. General procedure. A dispersion of 2.8 mmol of tetrazole I, 0.28 mmol of CuI, 5.9 mmol of ethylenediamine, 5.9 mmol of Cs 2 CO 3 , 1 3.4 mmol of halide, and 2 ml of DMF was stirred for 1 h (TLC monitoring of conversion) at 85°С in an argon atmosphere. The reaction mixture was cooled to 20°С and poured into 20 ml of water. The obtained solution was extracted with ethyl acetate (2 × 8 ml). The combine extract was washed with brine (2 × 8 ml), dried with anhydrous Na 2 SO 4 , the solvent was removed in a vacuum. The residue obtained was dispersed in ...

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Antimycobacterial derivatives of tetrazole

Cited by 8 publications

References 0 publications

Efficient synthesis of 1‐substituted‐4‐phenyl‐1, 4‐dihydro‐5H‐tetrazole‐5‐thione and (1‐phenyl‐1H‐tetrazol‐5‐yl)thioacetyl derivatives

Efficient synthesis of 1‐substituted‐4‐phenyl‐1, 4‐dihydro‐5H‐tetrazole‐5‐thione and (1‐phenyl‐1H‐tetrazol‐5‐yl)thioacetyl derivatives

Synthesis and Biological Evaluation of Quinazoline-4-thiones

New method of 5-mercaptotetrazoles functionalization

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